| 38.9% |
With hydrogenchloride; tin(ll) chloride; In water; at 65℃; for 2h;Inert atmosphere; |
Under nitrogen protection,5-(4-Nitrophenyl)-10,15,20-phenylporphyrin (1.91 g, 2.9 mmol)And stannous chloride (2.60g, 13.7mmol) was dissolved in concentrated hydrochloric acid (mass fraction 35%-38%, 190ml),React at 65C for 2 hours.After the reaction, the mixture was poured into ice (400ml),And neutralize with ammonia water (25%-28%) to about pH 8.The aqueous phase was extracted several times with chloroform until colorless, and the organic phase was dried over anhydrous sodium sulfate.After removal of the solvent with a rotary evaporator, a purple solid was obtained by column chromatography (eluent: petroleum ether/dichloromethane),That is 5-(4-aminophenyl)-10,15,20-phenylporphyrin (0.69 g, 38.9% yield). |
|
With hydrogenchloride; tin(II) chloride dihdyrate; In water; at 65 - 70℃; for 1.5h; |
A portion of the mixture including porphyrin 1a (30 mg) was dissolved in concentrated hydrochloric acid (80 mL). Tin(II) chloride dihydrate (2.6 g) was added, and the solution was heated at 65-70 C for 1.5 h. It was then cooled and poured into water (100 mL), and the resulting mixture was adjusted to pH 8 with concentrated ammonium hydroxide solution. The aqueous phase was extracted with chloroform. The organic phase was concentrated to a volume of 50 mL on a rotary evaporator, and this solution was chromatographed on a silica column eluting with chloroform. The second band eluted from the column contained the desired product. |
| 1.3 g |
|
A mixture of TPP (2.0 g, 3.25 mmol), trichloroacetic acid (26.6 g, 163 mmol), trifluoroaceticacid (7.2 mL, 98 mmol) and acetic acid (9.3 mL, 163 mmol) was placed into a 250 mL roundbottomflask. The solution was stirred for 15 min at 0 C. Sodium nitrite (561.2 mg, 8.13 mmol)was added in three equal portions at intervals of 1 h. Then the reaction mixture was stirred for 24h at 0 C. The reaction was quenched by adding water (30 mL) and extracted withdichloromethane (3 × 30 mL). The organic layer was then concentrated under vacuum to give thecrude product of nitration. The crude product was dissolved in concentrated hydrochloric acid (200 mL) and was stirred for30 min. Tin(II) dichloride dehydrate (2.7 g, 12.13 mmol) was added. The mixture was heated to80 C for 30 min. The water (70 mL) was poured into the reaction. It was then cooled to room temperature and stand for 24 h. The resulting green precipitate was obtained by filtration. Theprecipitate was dissolved in water (100 mL). The green solution was neutralized with ammoniumhydroxide until the color changed to violet. The resulting violet precipitate was obtained byfiltration and washed with water. The product was purified by column chromatography (silica gel,PE/EA, 4:1) to give the compound 2a (1.3 g, 63% yield). |
|
With hydrogenchloride; tin(ll) chloride; In water; at 65℃; for 1h;Inert atmosphere; |
Then, 150ml three-necked flask were added 500mg single nitro porphyrins, 50ml of concentrated hydrochloric acid, 1.31 g of stannous chloride (graded, without boiling together), nitrogen, reaction at 65 1h.The solution was adjusted to pH 9 with 1M sodium hydroxide, the solution was purple.Extracted with chloroform six times, 40 ml each time, dried over anhydrous sodium sulfate overnight.Spin-dry the solvent under reduced pressure, the crude product on silica gel column, eluent chloroform to do first with unreacted complete single-nitro porphyrins, the second with a single product for the target amino porphyrin |
| Ca.80% |
With hydrogenchloride; tin(ll) chloride; In chloroform; water; acetic acid; at 0.7 - 80℃;Darkness; |
In a two necked flask, 80 mg (0.121 mmol; 1 equiv.) of compound 1 is solubilized in 20 mL of CHCb. A solution of 82 mg (0.363 mmol; 3 equiv.) of tin chloride in 20 mL of HQ solution (37%) is added followed by 20 mL of acetic acid. Then, the reaction is carried out overnight at about 70C-80C, under agitation and in the dark. After cooling at room temperature, the mixture is neutralized with 150 mL of NaOH solution (2M). The crude product is purified by an organic phase extraction followed by washings with ultra- pure water. The final product, compound 2, is a purple solid obtained with a yield of about 80% (61 mg). |
|
With hydrogenchloride; tin(II) chloride dihdyrate; In water; at 80℃; for 12h; |
First, Adler method was used to synthesize tetraphenylporphyrin (TPP),Dissolve benzaldehyde (5mL, 50mmol) in 80mL propionic acid,Add pyrrole dropwise at 70C (4.2mL, 60mmol) propionic acid solution 20mL,The temperature was raised to 140C and the mixture was stirred under reflux for 1h. After cooling, 1.5g of TPP purple crystals were obtained by suction filtration with a yield of 20%.Further dissolve TPP (1.2g, 2mmol) in trifluoroacetic acid,Add nitrite (173mg, 2.5mmol) under low temperature (-15C ) to nitrify,The reaction was completed after 30min and extracted with dichloromethane,The solvent was removed by rotary evaporation to obtain the crude product,Column chromatography separated 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin 1.1g, yield 70%,Further dissolve 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin (1g, 1.26mmol) in 12mol/L concentrated hydrochloric acid solution, add SnCl2·2H2O (1.4g, 6.3 mmol) for reduction, heating to reflux at 80C for 12h, quenching the reaction with aqueous ammonia, extracting with dichloromethane, and removing the solvent by rotary evaporation to obtain a crude product, which was separated by column chromatography to obtain , 780 mg of 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, yield 92%. |
| 150 mg |
|
Conc.HCl (15 ml) was added to the RB flask, and 5-(4-nitrophenyl)-10,15,20-triphenylpolpyrine (195mg, 0.29 mmol) was added. After stirring for 5 minutes, a clear solution was obtained, Stannous chloride dihydrate (400 mg, 1.77 mmol) was added. The reaction mixture was refluxed at 65 C. for 1 hour under an N2 atmosphere. The reaction mixture was cooled to room temperature, slowly added to an ice solution, and neutralized with ammonium hydroxide. Extracted with DCM (2 X 100ml) to give a pink solution. The solution was distilled with a rotary evaporator to obtain a solid (TPP-NH2). Yield: 150 mg. |
|
With hydrogenchloride; tin(II) chloride dihdyrate; In water; at 70℃; for 5h;Inert atmosphere; |
Add 5.5mL of benzaldehyde to 200mL of propionic acid,After stirring, heating to the reflux of propionic acid,Slowly add 8.8mL pyrrole dissolved in 20mL propionic acid solution dropwise,After 40 min of reaction, the reaction solution was cooled to room temperature.100 mL of methanol was added to precipitate the product tetraphenylporphyrin,The reaction solution was filtered under reduced pressure, and the filter cake was washed with methanol to obtain about 2.2 g of purple solid porphyrin.The nitration of tetraphenylporphyrin was carried out in an ice bath,1 g of porphyrin was dissolved in 180 mL of dichloromethane,Add 6mL 65%-68% concentrated nitric acid,Then add 200mg sodium nitrite, after about 10min,Thin-layer chromatography showed the formation of a new major product,Add ammonia water to neutralize to neutrality, extract with dichloromethane,The nitroporphyrin (ie, 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin) was isolated by column chromatography.Under a nitrogen atmosphere, 500 mg of nitroporphyrin was dissolved in 40 ml of concentrated hydrochloric acid (its concentration was 35% to 37%),Then add excess reducing agent SnCl2 2H2O,Then heated to 70 C for 5 h,Then add ice water to the reaction system, neutralize with ammonia water to make the solution alkaline,After suction filtration, the filter cake was redissolved, and the solvent was removed by column chromatography to obtain aminoporphyrin (ie, 5-(4-aminophenyl)-10,15,20-triphenylporphyrin). |
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